In this paper we investigate nilpotenct and probabilistically nilpotent Hopf algebras. We define nilpotency via a descending chain of commutators and give a criterion for nilpotency via a family of central invertible elements. These elements can be obtained from a commutator matrix A which depends only on the Grothendieck ring of H. When H is almost cocommutative we introduce a probabilistic method. We prove that every semisimple quasitriangular Hopf algebra is probabilistically nilpotent. In a sense we thereby answer the title of our paper Are we counting or measuring anything? by Yes, we are.